Introduction:
“Young Cross Dressers Secrets”
*Sandy was busting at the seams to tell someone some very exciting secrets she was keeping. She couldn’t tell anyone she knows. She decided to tell them here.
__After reading “My Bra and Panties are Missing”, my own ‘real’ story kept nagging at me to be told, but I wasn’t sure how.
I decided to change all the names and write a story all about this secret world I stumbled into. I started getting very horny just thinking about all that had happened….
__My story also started with my younger brother I’ll call him Paul. I had my best girlfriend Tina sleep over one weekend when my parents were away. As girls do, we wore our skimpy nighties with no bras or panties. It made us feel free and sexy. I warned Paul to keep his mouth shut about anything that we did. We watched porn, giggled and did sexy dances around the house. We knew Paul was sneaking peeks at us and that made it all the more fun. We bet he was getting turned on by us.
Tina and I were going through our bi curiosity phase and at night were having our first ’girl sex’ experiences. What we didn’t know was Paul had first heard us and got turned on by it. Our rooms were next to each other and he listened through the furnace vent.
Tina and I had started our curiosities by getting under the covers naked and feeling each others tits. Next time we fingering each others pussys. Next time we got real bold, we turned and licked each others pussys. I guess we got a little noisy as Paul listened and wanked to our moans. How do I know that?….he told me himself.
We had a talk one day after school about sex. I sat on his bed as we talked he got a big tent in his shorts. This got me aroused to think that I was turning him on. Being so young, and being my brother, I never had any thoughts sexually about him….until now.
I laid down next to him. He and I both were getting aroused. We began to talk softly about the thrills of sex. His eyes were locked on my tits and my cutoff jeans. He told me about hearing Tina and I and what a turn on it was…. whatever we were doing.
His talk was arousing me more. He whispered that he wanked as he listened and It made him cum.
When he said that, I got my first pussy spasm from him.
Our parents came home and I jumped up and ran in my bedroom. I couldn’t wait to tell Tina what Paul told me. When I caught my breath and told her, her reaction was she wished he was a girl so we could have a threesome only with a guys cock to play with….Paul a girl?
I’d never thought about that. We talked about the next sleepover and fantasized about Paul joining us as a girl with a cock. We giggled about it, but real thoughts in our minds began to form. It was really turning us on to talk about a real threesome with Paul. We devised a plan.
After school that day, we went to a cross dressing porn site. We wanted to make Paul into a ‘Paula’. Young boys crossing dressing was a turn on for guy and girls?….it sure was for us. Paul was young and had the perfect body to be made up as a girl. Now to talk him into it.
It didn’t take much talking as the reward was to ‘maybe’ have sex with Tina who I knew he liked…. and ‘maybe’ even with both of us. When I approached him with the idea in his room, I noticed he got an instant hardon in his pants. He thought real hard, smiled said: “Ok”. Now It was set for this weekend.
Tina and I got a hot long hair wig, all the make up we had, a sexy bra, panties, panty hose for him to wear. Fingernail polish and the works. That night late, we got him in my bedroom and sat him at my dresser. We had him close his eyes and we went to work. He got sexier by the minute as we dressed and made him up to look like a sexy slutty type girl….except with a stiff cock in his panties. He was excited and breathing hard. We teased him by rubbing our hand on his smooth body. We let him feel our tits and pussys.
“Paula, you belong to us, we created you and you must do what we say.” I told him. We all giggled and had him stand up and open his eyes.
He was in sexual shock as he looked at ’Paula’. He felt his own tits and rubbed his cock. He reached under his skirt, went in his panties and felt his bare cock. He started to slow jack it. He was fully turned on. He was slow jacking while looking at ’Paula’ for the first time and he was liking this.
We stopped ’her’ and said we would take care of that. We all stood there and started a feel fest on each other. We turned down the lights and Paula looked even hotter. We told her: “Ooooo Paula, your such a sexy girl, we want to be your new girlfriends. We have girl sex and we want to have sex with you. We have to teach you about girl sex. We’ll have to feel you up first and you can feel us all you want.
Tina was real turned on and started kissing ’Paula’. She was feeling his nipples under his bra and rubbing the bulge in the front of his skirt. I joined in too as we started all making us real hot. This was so excitingly different, Paula was making my pussy all wet. I took ‘her’ hand and put it under my nightie to feel my wet pussy. Tina and I both went up her skirt to feel her stiff cock. We eased her panty hose and panties down over her warm cock.
Tina suddenly started rubbing her own pussy and grabbed Paula’s hand feel it too. I started for the first time jacking on Paula’s cock. Tina and I had never licked or sucked on a guys cock before. We dropped to our knees and shared licking on Paula’s stiff cock as we felt each others tits and pussys. Tina and I could make each other have little orgasms, but a big orgasm was building in us both now.
‘Paula’ told us later, her thoughts of what it was like for ’her’…..
“I went along with all this to ‘maybe’ get some sex from two girls, sis and Tina. This was weird, if my buddies ever found out, I would be branded ‘fag boy’ forever. I felt this was safe enough to let them make me up as a girl. I never expected to get horny over looking like a sexy girl. The transition from Paul, to ‘Paula’ was giving me a hardon. Having the girls change me into a sexy girl, I found it was easy to imagine I was a girl….a very horny girl with a hard cock.
It was exciting as the girls made me into ’Paula’, but when I opened my eyes and saw ’her’, ’she’ turned me on instantly. A girl I could feel and touch that was so sexy looking. I looked at her in the full length mirror and wanted to fuck a girl like her bad. I felt her tits and crouch. I had to go under her skirt to feel her stiff cock. I never realized what a turn on this would be, plus now I had not one, but three girls to feel up. I had to stop them from jacking on me as I was going to cum. I laid back on sis’s bed and let them play with Paula, while I played with them. Now ‘Paula’ wanted to fuck them both, real bad.
So this was the ’girl sex’ they were doing in bed during their sleepovers. I watched them feel each other up and now ‘Paula’ too. They got completely naked and rubbed their pussy’s together. They felt my tits and kissed me all over as they got themselves and me more and more turned on. It was so awesome getting a double turn on, as a girl and as a guy. They liked to put their hands up my skirt, go inside my panty hose and panties and feel my cock. They were super excited and took turns putting their pussy’s up to my face which I gladly licked. I knew now…. the pleasures of girl sex.
I got them to turn around so I could lick not one, but two pussys. It was the threesome from heaven, for now I was ‘Paula’ only I had a throbbing cock ready to explode.
I put my arms between their legs and took turns licking their wet pussys. They squirmed and moaned as they both jacked and licked my cock. I couldn’t hold back any more.
I shot cum like never before. They both moaned and took turns putting their mouths over the head of my cock. Their faces were both splattered with cum.”
—-
Paula’s tongue was taking Tina and I higher and higher when her cum shot out. Tina and I pushed out clits into his lips and both had the best trembling orgasm ever. We were ‘all‘…. totally hot for ’Paula’.
We all lay exhausted but soon Tina and I started in on Paula again. She excited us even more now. Feeling under her bra and rolling her nipples, tongue kissing her and feeling her cock started all over again. Paula was our personal toy and we loved making her hot for us. We whispered: (…“lick my pussy good Paula“…and.. “..suck on my tits, Paula.”..)
Tina and I both wanted Paula’s cock in our pussys.
Paula tells what it was like for ‘her‘…
“ I lay there with my blouse open and my panty hose and panties pulled down some. Tina was the one I wanted first. She was so sexy and was a hot tongue kisser. I was hot for Tina and wanted to fuck her bad. I rolled over on top of her, slid down and opened her legs wide. I licked my first pussy as she squirmed. Sis felt both our tits and our bodies. Tina was moaning and squirming as I slid up on her. She held my cock and guided in her tight pussy.
This would be my very first time to fuck a girl.
Sis moved around and put her pussy right up to Tina’s and my face. We both licked her pussy as we began to fuck. To lick sis’s pussy with Tina while Tina and I fucked was awesome….”
—-
This was Tina’s and my first time to have sex with a guy also. To be right there feeling and watching on them both as they fucked, had my pussy spasaming with both their tongues on my clit. Watching a girl fuck another girl was making Tina and I both moan with the high pleasure. Playing sex with Tina was a sexual high, but this was way over top on the excitement scale.
I watched Paula’s face get pink as she fucked Tina as hard as she could. She began to groan as she began cum hard. Tina was having her first big climax as she held Paula tight. I orgasmed right with them as they both licked my clit.
Watching and feeling their bodies bang together and both cum…. made me so horny, I wanted Paula’s cock in me now!
As they groaned and squirmed for a while, I began to feel Paula and Tina all over. Paula eventually rolled off Tina and I couldn’t get on top of Paula fast enough. I loved being naked on top of Paula. Her cock was still hard. I put it between my legs and now Paula was all mine.
Tina turned and now it was her turn to get her pussy licked by two tongues. Paula squeezed my tits and then my ass as I slipped her cock in my wet pussy.
Oh yes!…this was what I wanted. Paula and I wasted no time in licking Tina’s wet clit. Her body trembled with each dual lick. My pussy had never felt this good…. ever.
I could feel Tina’s fingers feeling Paula’s balls as we started moaning and slamming our bodies together. Paula started whisper moaning…(…“oh god, we’re all gonna cum, let’s make Tina cum…I’m gonna cum…cum with me…oh god here it cums…” I felt his balls pull up tight and my pussy tighten as…she groaned…and I shook as hot cum shot in my pussy. I squeezed Paula with every muscle I had. Tina’s pussy quivered steady as she climaxed with us…we all moaned and collapsed all locked together….
There is nothing more special than the first time.
—-
Now whenever we can all be alone, Tina and I call ‘Paula’ and ask if can come to my room and play….she always says ‘yes’. We have two more wigs and more slutty clothes we dress her in.
‘Paula’ and Tina read and approved of my story. Paula likes to read it out loud to us as Tina and I play…’girl sex’….then we pull her in my bed and have her fuck us. She never resists…..
Paul told his buddies that he had a step-sister living in the next town, named ’Paula’ and he was fucking her. The story sounded hot and they pretty much believed him. Tina and I told him in front of his buddies, that ’Paula’ is just a slutty tramp and he should stay away from her. That pretty well cinched it for them believing it….but…
(…as of now, none of them had actually seen this girl…‘Paula’….yet.)
—–
I was talking to Paul about our next time to all get together. He sat at his computer looking at pictures. I had him stop at a picture of a naked skinny girl, I looked closer, this girl had a cock. I said: “Oooo what a cute girl that guy makes. Who is that?” Paul said that was Benny, his best buddy. One day at Ben’s house he got out of the shower and as a joke, put on his mom’s wig and hi heels and came out naked to act silly for Paul. They both laughed as Ben walked around acting all girlish. Paul had his phone and quick snapped a picture of Ben. I looked at the picture more. Ben’s cock was semi-hard. I wondered if Ben was aroused by the wig and high heels he wore. I questioned Paul more about Ben.
Paul thought about Ben dressed as a girl. He began to smile. He said: “Could you girls handle another …cross dresser if I could get Ben to do it?” I said: “When do we start?”
Paul called Ben and said to come over. Ben was on his way. I had taken a picture of ’Paula’. Paul put it up on the screen. “Ben’s gonna shit when I show him this. He’s cool and won’t ever tell anybody because he knows I have that picture of him walking around as a girl.”
I quick called Tina to come over. Ben came over and was in Paul’s bedroom. We waited a while and then both went in Paul’s bedroom. Paul had worked fast and had Ben was trying on Paul’s wigs. Ben jumped and started taking the wig off. Tina and I stopped him. “Oh you need some help girl, let us help you….a….Betty.” Ben froze as we analyzed what make up to use on ‘Betty’. Paul had on his screen the picture of ’Paula’ and had already showed to Ben. Ben was shy and just sat there and then begin to smile at all that was going on. We all told him he needed to sleepover this weekend as our parents were going out of town. We said we had a hot girl for him to meet, named…“Betty“. Ben smiled and said: “…and one named ’Paula’?”
Ben knew where this was headed. As he thought about the ’risk’ and all, I pulled his head into my tits and said: “You like girls don’t you Ben?” He nodded his head. “You be here at 7pm, it’s all totally safe and secret what we do here.” I felt his smooth baby face and Tina felt under his shirt and felt his nipples. We knew what a sexy girl he’d make, we also noticed a bulge in his short pants. When he said “Ok’, Tina tongue kissed him as I rubbed my hand on his bulge.
At 7pm Ben was at the door with a bag. We all went up to my bedroom and we sat him in our ’make up’ chair. He opened up his bag. He made us all swear to keep this secret. He had wigs, bras, panties, dresses and high heels. Little Ben had been keeping a secret from…almost… everyone.
It seems that Paul knew every bit of Ben’s secret and being loyal to his friend, never told anyone.
As Tina worked on Paula’s make up I worked on ‘Betty’. They leaned over and whispered to each other. The now ‘Betty’ began to talk as we worked on them.
Ben said he got talked into putting on one of his mom’s wigs by his older brother Dan. His brother said he would never tell anyone…. ‘if’ Ben would leave it on and put on his mom’s bra, panties and a dress for his brother. His brother watched him and got all horny. He felt up Ben, and started calling him ’Betty’. He ended up jacking Ben off. Ben said he liked this and any time they got the chance, they did it more. As they progressed his brother got on his knees and sucked Ben’s cock. Ben liked girls, but now liked to cross dress and turn his brother on to get a blow job from him.
He said his older brother got him all this stuff if he would continue to cross dress for him.
Tina and I got all turned on listening to his story. Our minds were spinning with ideas of hot things to do with ’Betty’ now.
‘Paula’ and ‘Betty’ were all made up now. We stood them up and dressed them in sexy girls clothes. They looked at each other. Next thing we knew they were feeling each other up. ’Betty’ and ’Paula’ had never seen each other in person cross dressed. They were instantly turned on by each other. Two cocks now bulged out in their skirts. Tina and I lay on the bed to watch the show. They felt each others bodies, asses, cocks and tits. What a turn on this was to watch two girls with cocks turning each other on in this new secret world…….
Ben recalled what it was like that evening…
“I had never ever planned to share my cross dressing with anyone except my brother. I had no idea that Paul had gotten into it too. Now here I was looking at a picture of Paul cross dressed as ’Paula’ and his sister and Tina wanted to cross dress us both. Like Paul, I had never had sex with a girl, and I couldn’t pass this up to maybe fuck Tina, and Sandy. I had the hots for Sandy for a long time.
My heart was pounding away with excitement as Sandy put on my makeup. I could now see her bra-less tits through her nightie. If ’Betty’ turned her on I may get to have sex with her, and so far this was exactly what was happening. To add to the excitement, ’Paula’ was getting me horny looking at her. I watched Tina dress him and then feel ’Paula’ up. I was having a mega turn on with 3 hot girls to watch.
Sandy finished dressing me and started kissing my neck and feeling my tits. I watched Tina do the same thing to Paula, then they got naked and laid on the bed to watch us and feel each other up. That’s when Paula and I looked at each other and the fun began. We slowly began to feel each other up as we both watched Sandy and Tina rub each others pussy’s.
Paul and I had neither one ever felt another guys cock before….but as girls…it was all different. The desire to feeling a girls cock was a real exciting turn on. Paul and I were getting mega hot for ’Paula’ and ’Betty’.”
Tina and I, and all of us were at a peak of anticipation What is going to happen next. I wanted to be Betty’s first full sex and now was the time to act. Tina and I smiled at each other and sat up. I pulled Betty down next to me as Tina pulled Paula next to her. Betty was breathing so hard with excitement as I began to feel her body. We wasted no time in feeling us up. My pussy was getting wetter by the second.
My hand went inside her bra and found her nipples as Betty and I went to a furious tongue kissing frenzy. I inched up her skirt as she kicked off her high heels. I felt her sexy legs and kept going up. Her hand found my wet pussy and her trembling fingers went in my pussy. Her thumb was massaging my clit as our moans sounded so hot. My hand reached her panties and felt her bulging hot cock. I reach inside her panties and felt what I wanted so bad, her hot pulsing cock. It was just waiting to go in my pussy.
Tina was already feeling Paula’s warm cock and rubbing it on her pussy. The sound of four people moaning, tongue kissing, feeling each other was awesome.
I pulled an excited Betty on top of me. I raised my knees as she rubbed her cock on my open pussy. It slipped in so beautiful as we both gasp at the feeling. Our bodies meshed together as Betty’s cock went in and out of my pussy. We held each other tight and let our hips do the fucking we had waited for. I loved being fucked by Betty.
Tina and Paula were already fucking fast and slapping their bodies together….that sound just added to Betty and my peaking excitement. Deeper, harder and faster we fucked. Betty was squeezing my tits hard as it was about happen. I wrapped my legs around her raised skirt and my heels dug into her ass to drive her deep in me.
Betty’s body stiffened up as she moaned loud. I felt a huge shot of cum shoot in my pussy. We held each other tight as she pumped more in as I climaxed and shook. We just kept fucking and fucking to make the feelings last forever…..
We felt each others bodies as the room was spinning in my mind. Slowly we enjoyed the sound of Tina and Paula’s moans as Paula was licking Tina’s pussy as she squirmed in another world. I was out of breath as I managed to watch Paula climb up on Tina and put her cock in Tina’s waiting pussy. My pussy spasmed as they began furiously fucking. Betty was gasping as she started fucking me again. Now four people were fucking and moaning all together.
As we all began to moan and shake together, I hoped the bed would hold up to the glorious peak we were all having. The cum began to flow and climaxes peaking for our first foursome ever. Tina and I loved to squeeze their asses as we climaxed and they were cuming and banging their bodies on us. We lost it and semi-passed out as Paula and Betty joined us in the ultimate after glow…..
—–
I learned that Ben and Paul had a private talk. They both want to have sex with Tina and I as:
Ben and Paul, without the cross dressing. Tina and I took care of that desire one afternoon after school. We were all at Tina’s house. Her mom worked the late shift and no one would be home for a while yet.. Tina and I quickly paired off with me and Ben, and her and Paul. The guys were not expecting this and got hardons quick. It was an instant turn on with a time limit on doing anything. We all ended up right on the living room rug as buttons and snaps were undone. This was very hot and exciting for us all. Ben had my shorts down quick and his too. He squeezed my tits as I held his cock and eased it in my pussy.
It was a rush to cum and beat the clock. Our bodies thumped the wood floor hard as we all strained to keep quiet. I was very exciting to get that hot, that quick and no waiting. Ben and I were thrashing as we fucked furiously. The risk was driving us to fuck as fast as we could. Tina and Paul were trying to muffle their moans as Paul pumped on Tina as fast as her could. I saw Tina fingers squeeze Paul’s ass as they came together. Ben had his fingers on my clit, knowing this would make cum quick. We held tight as he shot his load in me as I climaxed with him. We all quietly moaned and were catching our breath when we all heard a key in the front door. We all scrambled up pulling our clothes up. Ben’s older brother Dan came in reading the mail. He eventually looked up to see us all sitting on the couch smiling. He said ’Hi’ and kept walking up stairs. We all held our hearts and sighed. That….was exciting, but was to risky to try that again.
We all agreed that fucking ’Betty’ and ’Paula’ was the most fun, but….with some Ben and Paul on the side…..
P.S.
Ben’s older brother Dan found the picture of Paul cross dressed. ’Paula’ now has a new boyfriend. Paul now does sleepovers at Ben’s house. Paul and Ben won’t tell me anything about what all they do, but …..they will…. and when they do…I’ll pass it right on to you…..

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